Cefaclor Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
Cefaclor differs from cephalexin primarily in the bio-isosteric replacement of methyl by chlorine at C-3 and is
quite acid stable, allowing oral administration. It also is quite stable to metabolism. It is less active against
Gram-negative bacteria compared with the other second-generation cephalosporins but is more active
against Gram-negative bacteria compared with the first-generation drugs.
Chemische Eigenschaften
white crystalline solid
Verwenden
Cefaclor belongs to the family of antibiotics known as the cephalosporins (cefalosporins). The cephalosporins are broad-spectrum antibiotics that are used for the treatment of septicaemia, pneumonia, meningitis, biliary-tract infections, peritonitis, and
Definition
ChEBI: A cephalosporin bearing chloro and (R)-2-amino-2-phenylacetamido groups at positions 3 and 7, respectively, of the cephem skeleton.
Antimicrobial activity
It is less resistant than other group 2 cephalosporins
to staphylococcal β-lactamase. It is active against
N. gonorrhoeae and H. influenzae and against most enterobacteria,
but it is susceptible to common enterobacterial
β-lactamases. Pr. vulgaris and Providencia, Acinetobacter and
Serratia spp. are resistant. B. fragilis and clostridia are resistant
but other anaerobes are commonly susceptible.
Clinical Use
Cefaclor (Ceclor) is an orally active semisyntheticcephalosporin that was introduced in the American market in1979. It differs structurally from cephalexin in that the 3-methyl group has been replaced by a chlorine atom. It issynthesized from the corresponding 3-methylenecepham sulfoxideester by ozonolysis, followed by halogenation of theresulting β-ketoester. The 3-methylenecepham sulfoxideesters are prepared by rearrangement of the corresponding 6-acylaminopenicillanic acid derivative. Cefaclor is moderatelystable in acid and achieves enough oral absorption to provideeffective plasma levels (equal to about two-thirds of thoseobtained with cephalexin). The compound is apparentlyunstable in solution, since about 50% of its antimicrobial activityis lost in 2 hours in serum at 37°C. The antibacterialspectrum of activity is similar to that of cephalexin, but it isclaimed to be more potent against some species sensitiveto both agents. Currently, the drug is recommended for thetreatment of non–life-threatening infections caused by H.influenzae, particularly strains resistant to ampicillin.
Nebenwirkungen
Apart from mild gastrointestinal disturbance, the drug is
well tolerated. Transiently increased transaminase levels and
symptomatic vaginal candidosis have been noted. Clusters of
a serum sickness-like illness have been described in children.
Sicherheitsprofil
Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: joints, dermatitis, increased body temperature. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Clí, SOx, an
Cefaclor Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
